Stephacidin B, the dimer of avrainillamide, is green pigment isolated from Aspergillus ochraceus and other Aspergillus sp. Stephacidin B is more potent and selective than its monomeric analog, stephacidin A. Stephacidin B is rapidly converted to avrainillamide in cell culture. This natural alkaloid is used in cancer research.
Stephacidin B is soluble in methanol or DMSO.
| Molecular Formula | C52H54N6O8 |
| Cancer Applications |
Stephacidin B was reported as a potent antitumor agent by Bristol Myers Squibb (2002) against testosterone-independent PC3 and testosterone-sensitive LNCaP prostate cell lines with IC50 of 0.47 and 0.06 µM respectively. Stephacidin is active against sensitive and resistant ovarian, colon and breast cancer cell lines. The stephacidin family of of natural anticancer agents are active against the human colon HCT 116 cell line. The signature bicyclo [2.2.2] diazaoctane ring system common to these alkaloids has inspired many synthetic approaches. |
| References |
Escolano C (2005) Stephacidin B, the avrainvillamide dimer: A formidable synthetic challenge. Angew Chem. Int. Ed. Engl. 44(47):7670-7673 PMID 16252300 Qian-Cutrone J et al (2002) Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells. J. Am. Chem. Soc. 124:14556 Wulff JE et al (2007) The natural product avrainvillamide binds to the oncoprotein nucleophosmin. J. Am. Chem. Soc. 129:14444 Wulff JE et al (2007) Evidence for the rapid conversion of Stephacidin B into the electrophilic monomer avrainvillamide in cell culture. J. Am. Chem. Soc. 129:4898 |
